I want to claim your cunt and cover you in my cum.
Of all the flirty texts I used to dream about exchanging with my middle school crush, this one surpassed my wildest fantasies. And yet, here I was over a decade later, smirking at my phone screen and sending an angel emoji in response to Drew*, my childhood bestie’s older brother, on whom I’d had a major crush between the ages of 11 and 13. Five years older than me, he’d never thought of me as anything more than a playmate for his little sister—until tonight.
Back in my hometown for the holidays, we’d bumped into each other earlier that day at the grocery store when we both reached for the same pound of butter. It was as if the writers of our lives had suddenly started working for the Hallmark channel—though Drew and I had far less PG plans in mind.
Now thirty, Drew was even more handsome than I remembered. He had wavy brown hair and kind, bespectacled eyes. He was thoughtful and a good listener—mental notes I’d taken while we were stuck in the checkout line together for nearly half an hour, inching forward as we caught up on each other’s lives. There was immediate chemistry between us, and we both knew it.
Now, four hours later, I was sexting my fingers off in my parents’ basement and making actual plans to put our fantasies into action. There was just one problem: he was sharing his apartment with some cousins from out of town, and my place was…my parents’. But Drew offered to use some hotel points he’d collected to book us a room the night after Christmas. Once the plans were made, all we had to do was wait.
Of course, that part was torture. The entire next day, all I could think about was Drew’s hands on my body. I wanted to feel his weight on top of me. I wanted to feel him in me. I wanted him. Badly.
The anticipation was like a drug to me. When the time came, I got into my used, beat-up sedan and drove myself over to the mid-priced hotel chain where Drew had gotten us a room. I parked next to his car, the dark green hatchback he had told me to expect, and texted to let him know I was there.
Room 312, he texted back.
The walk across the parking lot was daunting, and I wondered if he could see me from the window. I actively tried to keep my cool in case he could, but mostly I was a puddle of arousal and suspense.
Room 312 was at the end of a long hallway, in the corner of the floor. I stared at the door for a long second before tapping my knuckle against it three times. Before I could catch my breath, he opened the door and greeted me with a warm smile.
“Come on in,” Drew said, taking my hand. His palm was warm against mine in a way that made me want to press more of myself up against him. He released me, only to take my jacket and hang it over the chair by the desk. Anticipation ate away at me until he stood in front of me, stepped in closer, and captured my lips in his.
He tasted like spearmint as we kissed. His right arm twisted around my waist, pulling me into him, while his left hand rested at the base of my scalp, tilting my head back for better access.
“I’ve wanted to do that for forty-eight hours now,” he admitted.
“Me too,” I sighed. I ran my hand down the length of his torso, acutely aware of how muscular his lean body was and just how hard he grew between us. “Do you want to sit on the couch?”
He did, and I put one knee on either side of his hips, kneeling in his lap. “Is this okay?”
He leaned forward, peppering my cleavage with light kisses as his hands cupped my breasts through the lacy bralette I wore under my dress, lightly squeezing my D-cups through the fabric. “Mmmm.”
I could feel his cock twitch between my thighs and tilted my pelvis, rocking back and forth to encourage him. He groaned as I rolled my hips against him. I thought he was enjoying himself, but he quickly moved me off of him and onto the couch.
“What’s the matter?” I asked, concerned.
“You…you’re irresistible to me,” he said. “You feel like playing with fire…and neither of us has even taken any clothes off.”
“We can slow down,” I offered, afraid I had been too aggressive.
“Unh-unh,” he said, extending a hand in my direction. I took it, and he pulled me in so we both stood looking at the bed. “Undress,” he commanded.
I did as instructed, untying my wrap dress behind me and letting it fall open. He slid it off my shoulders, then gently undid my bra clasp. I hooked both thumbs in either side of my panties, bending down to remove them, then turned to look at him.
“Holy shit, Emmy.”
He paused, then brought his lips close to my ear again and whispered, “Get on the bed.”
I lay on my back, my legs half-spread as he stood over me. I couldn’t help but let a moan escape my lips as he leaned down and let his fingers drag up and down my slit.
“I want you so wet on my cock,” he growled, primal instincts taking over, his fingers lightly flitting over the shaved-smooth skin. “I want you absolutely leaking for me.”
“I’ll do my best...”
“No,” he said. “If you’re not the wettest you’ve ever been, I’m not going to fuck you. Do you understand?”
I nodded, moaning as he pressed himself against me, circling my clit with the head of his cock. I could feel how wet I was when he pulled away, replacing the touch of his cock with his fingers.
“I need you,” I begged, hoping that what he’d just felt could sway him to put aside his mission to make me the wettest I’d ever been and just fuck me right now. “I need you inside me.”
“Not yet,” he said as he made his way down my body, kissing my thighs and dragging his teeth against them in a way that made me wish he would just take a bite out of me.
From my thighs, Drew kissed his way up to my clit, slowly darting at it with his tongue. He alternated long and short strokes, and the sensation was indescribable. He was forever raising the bar with his enthusiasm and skill.
He leaned back for a second and I glanced down to see him looking pleased with himself. His eyes flickered up to mine and he grinned. “Your pussy tastes really fucking good, Emmy.”
“You’re doing it justice then,” I moaned as his fingers entered me and curled inside. He hooked them up against my most sensitive spot, coaxing a deep groan from somewhere within me that I didn’t know existed.
We found a rhythm together, his fingers thrusting in me as I raised my hips to meet the movement of his tongue. I wanted as much of him as I could get and I wasn’t afraid to be greedy.
“I’m gonna make you cum so hard,” he said between a series of long, flat brushes of his tongue. “You’re not even going to know your name.”
I laugh-moaned, infatuated with this idea of his as pressure grew inside my pelvis in a peculiar way. I wasn’t sure what was happening, but it was quickly all too much to handle. As I started to orgasm, I threw my head back and let out the loud, uninhibited moan I was barely managing to contain.
Suddenly, his face and my thighs felt soaked, and my breath hitched. Had I just…squirted? I was still enjoying the high of my orgasm, but I was also deeply confused. Drew massaged my legs, convincing me to enjoy the fading twitches and spasms that he’d worked so hard to achieve.
He laughed, a good natured noise that reassured me. “Emmy, you should’ve told me you were a squirter.”
“I didn’t know,” I said breathlessly. “I can’t believe that just happened.”
“No way,” he said, rolling off the bed and wiping his face off. “I don’t believe you.”
“Mmhmm,” I murmured. I felt drained— in a good way!—but I was still totally worn out by how hard I’d cum.
“Let’s give you a bit of a break then, huh?” Drew said, sliding in bed behind me and wrapping himself comfortably around my hips.
I could feel him, half-hard against me in my post-best-orgasm-of-my-life haze. I drifted off to sleep with Drew’s arms around me, wondering what my middle school self would think if she could see me now.
*Name has been changed.
